Recent shots of a craggy Mick Jagger performing in a graphic-print black and white jacket with matching Stephen Jones trilby call to mind a 1963 portrait of The Rolling Stones. Dressed in clean cut hounds-tooth suits, all bowl cuts and Chelsea boots, the photo was taken by Philip Townsend during the group’s blues-band incarnation. Sartorially speaking, much has changed since then for the Stones, who marked half a century in the music business by headlining the Pyramid Stage at Glastonbury on Saturday. “Can’t wait to play Glastonbury,” Jagger tweeted in the days leading up to the gig. “I have my wellies and my yurt!” Rubber boots and canvas hardly evoke images of Jumpin’ Jack Flash – but then again it’s best to be equipped.

When they first emerged in the 1960s, The Stones were pitched as Byronic bad boys to the ‘clean-cut’ Beatles (in truth, their off-stage appetites and excesses were not dissimilar). Regarding frontman Jagger, it was his compelling combo of pouty lips, distinctive vocals and post-Presley gyrating that drew the eye, his style evolving through the decade from sharply tailored suits – most likely inspired by his Mod-like bandmate Brian Jones – to flowing flares, billowing blouses and spiritual ensembles. The Swinging Sixties saw Jagger enter a foppish, dandy phase, sporting top hats, scarves, jewellery, ruffled shirts and velvet coats. This almost androgynous look, with its Sun King flamboyance, pooh-poohed the priggish, masculine codes of the establishment. Combining camp with cockiness, Jagger’s aesthetic was at once virile and feminine, much like fellow rock star Jimi Hendrix and, in later decades, Prince.

The middle-class singer always had natural panache, working as hard on his wardrobe as his ‘mockney’ accent. He commissioned a number of suits from Savile Row-revamper Tommy Nutter, who dressed him for his wedding to model Bianca Pérez-Mora Macías in 1971. Indeed, one iconic image of Jagger, taken by Richard Hamilton following the infamous 1967 Redlands drug bust, has him handcuffed yet dressed impeccably in a peak-lapelled green velvet jacket with striped tie. (Faithfull reportedly wore just a fur rug.) Another sees him, two years later, in a gender-bending white poet’s robe at the free Stones in the Park concert, during which he quoted from Shelley’s elegy to Keats in tribute to the recently deceased Jones – found drowned in his swimming pool just 48 hours earlier. Hundreds of cabbage white butterflies were released in Hyde Park after the reading.

Jagger and Faithfull, Jones and actress girlfriend Anita Pallenberg were Pied Pipers of their age, with slavish followers of fashion aping their looks – long coats and dresses, fitted-but-flared velvet suits, printed shirts and suede boots – by scouring boutiques on the King’s Road, Carnaby Street and Kensington Market. The primped and preening Jagger was one of the frontrunners said to have inspired Carly Simon’s 1973 hit ‘You’re So Vain’ – although his backing vocals indicate he wouldn’t have taken such an accusation as any kind of slight. For while he got off on appearing ambisexual – he and gay ballet dancer Rudolph Nureyev could have been twins, and mixed together socially – his heterosexuality was rarely in doubt, due to a penchant for being seen with catwalk queens. In addition to Faithfull and Pérez-Mora Macías there was Chrissie Shrimpton, Marsha Hunt and Jerry Hall, whose relationship with Jagger lasted a remarkable 21 years – until lingerie model Luciana Gimenez gave birth to his seventh child.

Smart casual

For Glastonbury, his stage attire will have been planned with input from current partner L’Wren Scott, an American fashion designer whose studio just happens to be on the King’s Road. Marrying casual and glam elements, in line with Jagger’s getup thus far for The Stones’ 50 & Counting world tour, his main look paired a bold emerald and gold sequined tux jacket with custom super-lightweight and stretchy black J Brand denim – all the better to strut in.

As the godfather of the skinny jean, the singer has always favoured slinky looks cut to flatter his athletic, rail-thin physique. Where songwriting (and sometime sparring) partner Keith Richard happily maintains a hellraiser reputation, Jagger is now more renowned for his fitness and clean-living ways. As he prepares to turn 70 in July, he’s reportedly a voracious vitamin popper who, when not touring, likes to be in bed by the distinctly un-rock’n’roll hour of 11pm. His beauty regime is said to include superjuice smoothies, oxygen treatments and lashings of Crème de la Mer skin cream. To this end, Jagger seems to have found a soul mate in Scott, once described by The New York Times as having a “sense of discipline that would rival a headmistress”.

Jagger also likes to tailor his costumes to their context. “When you’re on stage [the costumes] have to fit, and they have to be – for me – glamorous,” he told Women’s Wear Daily prior to the kick-off of the 50 & Counting tour in November. “They have to fit in with the show. If you’re doing a small club, like we did the other week [two secret club gigs in Paris], you don’t want to dress up like a popinjay. If you’re playing in a really big stadium, you want to be in super-bright colours, otherwise you just get lost. But if you’re in an arena that’s really well-lit, like we’re going to be in the next few shows, you don’t have to be Day-Glo.” He now limits costume changes to tops, swapping a purple silk shirt for a cropped glitter jacket atop a sparkly black shirt or a silver python-skin jacket and matching tie. While delivering a hint of glitz for the all-ages crowd, it’s tame compared to the chest-baring, rhinestoned glam-rock Ossie Clark jumpsuits of yore.

Style aside, comfort is now a key consideration for Jagger. L’Wren Scott introduced him to cult designer Rick Owens’ soft, near-weightless t-shirts and he also favours springy black Nike Air Max shoes which, with their raised wedge heels, help close the five-inch height gap with his 6ft 3in (1.9m) partner. It perhaps explains why he now wears those trainers everywhere – including red-carpet events, where they’re paired with a bespoke suit by Scott or Timothy Everest, and a white shirt. Neither dress-code nor age appropriate, they’re a cheeky nod to his inner rebel but maybe put paid to the kind of endorsements that have been coming Richards’ way. Recently tapped to star in Louis Vuitton’s ‘core values’ campaign, alongside Mikhail Gorbachev and Angelina Jolie, the guitarist is wearing Saint Laurent on tour – a collection of bespoke accessories and shirts by designer Hedi Slimane.

As the frontman of the world’s most enduring rock band, Jagger has seen his influence echo through generations; One Direction’s Harry Styles now carries his libidinous mantle (and messy coiff) but as yet demonstrates little of his creative brilliance, while endless groups have aped The Stones’ sound, style and debauchery with varying levels of success. Yet put him in a crowd at cricket match (he’s an avid fan) in casual-chic civilian mode and you’d have a hard time identifying him. If anything, it’s that open-mouthed pout – inherited by cover-girl daughters Elizabeth and Georgia May – that has the strongest resonance, as the inspiration for a design-classic logo that will surely outlast even The Stones themselves. Style is hardwired into Jagger’s DNA.

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